The Sexcapades of Squirrel
by mischief-maker1
Summary: A series of one-shots featuring Dean doing what he does best...after hunting, of course! Warnings at the top of each chapter. Dean/OFC OR Dean/Reader Insert
1. Love Shack

**Disclaimer: Nope. So sorry. You didn't stumble upon Eric Kripke's fanfiction. LOL.**

 **Author's Note: HI ALL! So, if you follow me on tumblr, (same name, btw. Come see me!) You knew to expect this...My friend, Gina, and I are embarking on a lovely little series of one-shots based off sexual experiences Dean has. This actually started with my Dean/Reader Insert story for the GIEPP over on Tumblr, which I'll post on here as well. I told G about it and she decided to write something. She sent me a dark!Dean story (which I am going to post, but not here. It's too dark and there are too many warnings.) Anyway, after talking, and she and I discussing additional ideas, we decided to join up and write a series of one-shots. So, this one is mine. Next up is hers...I think. I'll let you know as I go.**

 **So, here we are...hope you're ready for some sexcapades! Ready for Dean's first time? Hehehehe.**

 **Warnings: Smut, obviously, one spank, mentions of John being mean to Dean, First time, virgin!dean, experienced!girl. Both characters are under 18. NO DUBCON or NONCON. Just a fun little ditty. Hope you like it!**

* * *

 **The Sexcapades of Squirrel**

 **Chapter One**

 **"Love Shack"**

Dean walked into the grocery store with a cool twenty in his hand. His dad had told him to get some food for himself and to make sure to buy snacks and stuff for the following week for Sammy. But for two whole days, Dean could eat what he wanted, do what he wanted. Their dad was taking Sammy out to hunt a vengeful spirit and do some practice drills. John had noticed Dean had been taking the lion's share of the work and Sam had begun to rely on that. Well, why shouldn't he? The kid wasn't eleven for two more months! But the two other Winchesters were going to be gone, leaving fifteen year old Dean to his own devices. And right now? Ogling Tiffany Spangler, the prom queen, and buying himself a box of Lucky Charms to eat his way out of were his biggest plans. He was also gonna try and see if he could maybe hear or see something on one of the blurry porn channels on the motel's TV.

He had yet to do the deed...most girls his age, well, they were still young enough to wanna hold onto their v-card, and the older girls...weren't interested. That didn't mean his hand hadn't been his best friend in that department for the past two years.

He heard the bell above the door jingle as he walked in and he glanced around, cautious, like his dad had taught him. He picked up a basket and quickly gathered his items before slowly walking back up toward the front. Sure enough, Tiffany was working. This was her parent's store and she was forced to work in it for her "moral fortitude" or so he'd heard. He wasn't entirely sure Tiffany knew what 'moral' or 'fortitude' meant.

She was popping her gum in that half annoying/half sexy way girls would do and she was twirling her hair around her finger as she talked on the phone while checking out customers. He strained his ears and heard her arguing. "Damn it, Jason! You know my parents are going out of town!" She paused, then growled, "Fine! See if you get in my panties ever again!" Dean jumped at the sound of the phone slamming down onto its cradle and he smirked. Jason Richardson was the captain of the football team. He was also a major dick. Dean had heard he'd gotten caught doing something...inappropriate with the local preacher's daughter. His parents had shipped him off to church camp for the weekend.

Dean only knew this because he kept his head down and his ears open. He wasn't quite filled out yet. The freshman girls giggled and cooed around him, and of course, the girls in Sam's class looked at him with their hearts all a flutter, but older girls? Nope. Nada.

He swallowed hard and took his basket of goodies to Tiffany's line. The store wasn't busy. They were staying in a small town in Nebraska. John had left them alone quite a bit and it had become their home base for the past couple of months. He didn't have friends, but Sam did, and that was the main thing. The kid was on the book-a-thon team and had gotten honor roll, too. Dean couldn't have been prouder of his baby brother.

Tiffany glanced at him and narrowed her eyes. "You go to my school, don't you?"

Dean blinked in surprise that she was even talking to him. "Y-yes." He cleared his throat and tried to get his voice to go down an octave. "Yeah, I do," he tried again. Better, but he still sounded like a damn kid.

She continued to eye him speculatively as she rang up his purchases, smacking on that damn gum. Dean was fascinated as he watched her mouth move. "You're cute," she told him, finally.

He felt the blush run up to his cheeks, to the tips of his ears, then down his neck. "S-So are you."

"You got a name?"

"Dean," he managed.

She blew a bubble and said, "That'll be ten twenty-seven."

He handed over the twenty and counted out a dime, nickel, and twelve pennies from his pocket, quickly added up how much a double cheeseburger would cost from the diner down the road. That would be heaven if he could get an awesome cheeseburger and fries.

She handed him his change and eyed him again. "Are you a virgin?"

He blinked and wished, just for a minute, he could melt into the floor. "Wh-What?!" he squeaked.

She smirked. "Thought so."

"Hey, I have you know..." he started, but she leaned across the counter, pushing her breasts up slightly as she leaned on her folded arms before she put her finger on his lip.

"Don't try to bluff, I know a scarlet V when I see it." She smirked. "My weekend plans just fell through. Want to come over to my house? Let me rid you of that albatross and show you what a girl really likes."

His brain short-circuited. "All I wanted to do was enjoy being alone this weekend. My dad and brother are out on a hu-uh, I mean, they're gone for the weekend."

Her lip quirked. "So...what? Spending time fisting your junk is better than having it sucked on by me?"

He swallowed again and rubbed his erection against the wall of the counter. He was gonna cream his pants if she didn't stop talking. "I-uh...no! Of course not!"

She smiled. "Great. Then come by my house tonight at seven. And, uh, here..." She reached over where the cans of pineapple were on sale, three for a dollar. "Eat this."

"Wh-Why?" he questioned as he took it.

"I read it makes your jizz taste better. I wanna find out if Cosmo was right or not."

"Really?!" Damn. Had his voice always been this high?

She giggled. "Oh, the things I'm gonna teach you..."

"Do I need to buy...?" Holy shit. Did he need condoms? Lube? What did a person actually need for sex, anyway?

She shook her head. "I've got condoms...and other things we will need. Trust me. I got you covered."

He swallowed hard one more time. "Al-Alright. See you tonight, Tiffany."

She winked. "Oh, and rub one out before you come over, okay?"

"Wh-Why?"

She rolled her eyes. "Can't have you blow your load too soon, alright?"

"Will I...are you sure?"

To his surprise, she leaned across the counter and put a hand in his face. "I'll take care of you, Dean. I promise."

He nodded and walked blindly out of the store, almost running into the door in his way out. He had a lot to process in the next few hours.

* * *

At seven, sharp, he arrived on Tiffany's doorstep. He'd had to walk over, but luckily it wasn't unbearably hot yet so he didn't have to worry about pit stains. And he'd used a bunch of deodorant. And taken a shower. And rubbed one out. Well, okay, two, because the cold shower didn't help, and now his palms were sweating. But he swallowed hard and rang the bell.

She opened the door in a tiny tank top and and even tinier shorts, much too little clothing for the chilly March evening. "Fuck," he murmured under his breath.

She chortled and held the door open. "We'll get to that soon enough, tiger. Come on upstairs."

"Al-Already?!" he exclaimed.

She rolled her eyes. "Unless you want to talk about the Gulf War and President Bush's decision to go in, which is an interesting discussion at the right time. I'm planning on being a journalist. So, I'd be interested in your thoughts on the subject, however, I suggest you follow me."

He licked his lips nervously. "Oh-Okay."

She smiled and grabbed his hand. "Come on, Dean. I won't bite. Yet."

He followed her blindly up the stairs and into her room. He glanced at her canopy bed and his eyebrow rose.

She smiled. "Daddy still thinks I'm his angel." She pouted prettily. "You won't tell him I'm a devil, will you?"

He chuckled. "Your secret's safe with me."

She nodded. "Good." She appraised him. "Strip."

He blinked. "Excuse me?"

She smirked. "Strip. Trust me, Dean."

He nodded and began taking his clothes off, ignoring the shaking of his hands. He was going to do this. His dad had given him the talk and gave him a condom to use in case the urge struck. But that had been over a year ago. Did condoms expire? He probably needed to check into that.

He stood tall as he finished undressing and watched her appraise him. He knew he was decent looking. He'd recently started lifting weights in addition to his dad's training. He was still kind of skinny, but at least he was starting to fill out.

Her eyebrow rose. "Not bad. Yep. You're definitely cute. Give you a few years and you'll be smoking hot. Girls will throw themselves at you."

His chest puffed out at that.

She smirked and sidled up to him, careful not to touch him. Her voice was soft, low and dangerous as she said, "Let me show you how to fuck, and you'll have girls eating out of your hand."

"Okay," he breathed.

She leaned back and walked around him. "See, it's not enough to have a pretty face, not enough to have a good body, you gotta show you know what you're doing, and not be a total dick in the sack. Wanna turn a woman off? Don't give her hers. Trust me; we've got radar for that sort of thing." She brushed her fingers over his knuckles. They were bruised from a training session with his dad. He was getting better. He'd managed a good few hits, earning a grunt of approval and a war whoop from Sammy. "It's not enough to be a fighter," she told him. "You gotta be a lover, too."

He nodded reverently.

She smiled and her fingers trailed over his back, down to the slight curve of his butt. "My god, you've got a nice ass for a boy."

She came around to his front and the question he'd been dying to ask, popped out of his mouth. "How do you know so much about sex?"

She chuckled. "Sweets, I've been doing this for a few years. And very few of my lovers have been teenage boys"

Dean's mouth fell open. "You mean..."

She smirked. "Coach Miller? Let's just say he knows about a hell of a lot more than just how to conjugate a verb."

Dean couldn't believe it. Even being a guy, he knew Coach M was a good looking guy. All the girls talked about him. But Tiffany had actually...

He gasped as she grabbed his cock, knocking him out of his thoughts. "The hell?!" he growled.

Instead of answering, she merely dropped to her knees and gave him an experimental lick before she sucked him deep. "Gah, fuck..." he whimpered.

She pulled off of him with a "pop" and sat back on her heels as she looked up at him. "Okay. So, here's your education in blow jobs. Rule number one. NEVER fuck her mouth. You let her lead unless she tells you different. Getting head is a privilege. Repeat that."

"Getting head is a privilege," he repeated and then gasped anew as she seemed to swallow his Johnson whole. His hand reached out and he gently put a hand on her head, massaging her scalp lightly. She hummed and it went straight through him, making him grit his teeth in pleasure as he sucked in a ragged breath. "I...Tiffany..."

She pulled off and looked up at him again. "I like that. Good job, Dean," she praised him with a smile. "Now, I don't mind you pulling my hair a little bit, just don't get forceful. Oh, and, word of warning, I'm a swallower."

"What do you-" but thought left him as she dove back onto him, sucking him like a Hoover, not letting up until he felt it, he was going to... "Christ!" he screamed as he came. She swallowed around him a few times and released him. He staggered until he all but fell onto her bed. "Sweet fuck," he managed as he sat.

She giggled and wiped her mouth daintily. "Was that good, baby?" she purred.

He nodded fervently. "I had no idea..." He shook his head in wonder. "My hand will never do it for me again."

She smirked. "Trust me, you'll have to use that more than you'll get a girl's mouth. Now comes the hard part."

He smirked this time. "Pretty sure I was already hard once," he told her.

She laughed throatily. "Cocky? I like that." She pushed him down and straddled him, still fully clothed. She leaned down onto him and just barely kissed his lips. "Now, we move on to kissing."

"I thought we were gonna have sex...?" he inquired, confused.

"Rule number two; foreplay is the most important part."

His brows furrowed.

"Look at it this way; you wouldn't go down a dry water slide, would you?"

He'd never been on a water slide, but the comparison made him wince. He'd been down slides before, when he was younger, that burned his legs and scraped and he had to do that butt scoot thing to make his way down. It was less than fun. Was that what it was like for a girl when...?

She smiled. "I see that light bulb going off in your head. Okay, so, we make out a little bit, work on your kissing skills, get me wet and ready..."

That was all it took for him to start getting hard again. She reached a hand down and pumped him a few times. "Trust me. We'll get there. But first...making out..."

She showed him how to kiss, how not to use too much tongue, how to slowly (and gently) grope her through her clothes, making his way to second base, taking his time as he slowly moved over her body until she was gasping and panting in want as well.

"You're good," she mused breathlessly. "You've got some damn good natural talent."

He smiled. "Thanks."

She stood and looked him over. "Wow, you're so pretty."

He blushed, just slightly. Guys weren't supposed to be pretty, were they? But the way she was looking at him, surely that couldn't be a bad thing, could it? But then those thoughts fled as she slipped that tiny tank off and slid those shorts down her impossibly long legs and then she was dressed in only a pair of blue satin panties. He swallowed hard as she slunk back over to him. She smiled as she kissed him again. "Now, you can play with my tits. Just like over the clothes, don't be rough with them. Kiss them. Lick them. Suck them. Gently. If a girl wants it rough, she'll encourage you. Trust me."

He nodded and she laid back down next to him, on her back, and she tugged him on top of her. "No sex," she commanded. "Just...get my motor running."

He licked his lips and they continued making out. He felt...he felt like doing more. So, his hands roamed down to those blue satin panties and he rubbed her, between her legs, over the top of those panties, feeling the satin slip and slide against his hand.

"Oh, God, yes," she whimpered. "I like that."

He grinned at the fact he was doing something right and continued gently rubbing, teasing her. "Put your fingers inside," she instructed.

He froze. She smiled up at him and guided his hand under her panties. His fingers brushed her lower lips causing him to clench his jaw and force himself to think about salting and burning a rotting corpse to control his urge to rut against her leg and come like the virgin he was.

"Slow and easy at first," she instructed. "One finger at a time, then, there," she said as his finger touched a harder little nub. "That's my clit. Pay special attention to that, but not too much. Circular motions work for me, some girls like it up and down. Trust me, you'll know if they're happy."

"Girls like this?" he asked in awe.

"Some more than others. Just go slow, and always let her lead you. You let her lead you, and trust me, babe, she'll do just about anything you want her to."

He let her guide him as he slipped one finger inside of wet heat, pumping it slightly, in and out. "Add another finger," she told him, and he complied. "Damn. You've got big fingers and you're not even finished growing."

He chuckled and put his mouth to her breast again. He felt her fingers grip his hair as her hips began to move. He continued pumping his fingers as his mouth began exploring her breasts, her neck, her collarbones, up to her face, her lips, then he could almost feel it, his fingers were causing something within her. Her hips continued to move and she moved his hands slightly, guiding him wordlessly to get her where she needed and then suddenly, he felt her wetness drench his fingers as her inner muscles clamped down on him and his eyes grew wide. "Holy shit," he whispered. "Did you just...?"

She licked her lips and smiled. "Lots of natural talent."

He smiled down at her. "Wow."

She giggled. "Do you want to take a breath, or...?"

He eyed her. "What's the next lesson?"

She smirked and tugged his hand out of her panties. He marveled at the wetness clinging to his fingers. He did that. He caused that. Awesome.

"Lick them," she commanded.

He blinked. "What?"

"Your next lesson? Cunnilingus."

He'd read enough about sex to know what that was, but he wasn't so sure...

She smirked at him. "Think of it as Gatorade without the flavoring. It's salty, a little tangy, and delicious."

"How would you know?" he asked.

She just chuckled. "Who said all my a sexual experience was with men?"

His eyes widened. "You...you're gay?"

She laughed out loud. "Oh you poor sweet innocent thing. No. I'm bisexual. I like guys and girls."

"That's...is that a real thing?"

She smiled and nodded. "Most definitely. So believe me when I say I know what to teach you. Now, lick those big beautiful fingers of yours."

He swallowed and took a tentative lick to one digit. She was right. It was a salty flavor, tangy. Really, he kind of liked it. He licked each finger by turn and then turned his gaze toward her. Her pupils were blown and she was breathing in little huffs. He smiled. "Does that turn you on?" he asked, half in amazement, and half in boastful bravado.

She nodded vehemently. "Yes," she panted. "Damn, that's sexy." She slipped her panties down and off her legs, flinging them in the direction of the door.

He maneuvered himself so his shoulders were settled between her thighs. "Okay, so...what do I do?"

"Just like with making out, make out with my pussy. Lots of tongue, and, if you want, you can use some fingers inside, easy, like you did before."

He swallowed hard and eyed her lower lips, pink and glistening with her come. He looked back up at her. "You're sure?"

She nestled back against the pillows. "Definitely."

He took one langue lick and he felt her shiver. "That...that's good. That's so good, Dean," she told him as her hand fisted in his hair, tugging slightly.

He began rubbing his cock on the sheets, moving his hips in time with his tongue and it felt awesome.

"Are you playing with yourself down there?" she asked in a chiding tone.

He pulled away from her and looked up. "No. Of course not."

"You can, you know. Fist that sexy cock of yours in your hand. Get yourself off while you're getting me off. Just make sure to pay more attention to me than yourself. Trust me, I'll make it good for you, too."

She kept telling him to trust her. Did she think he was gonna stop now, with his mouth buried in her pussy? He didn't ask. Instead, he did as she instructed, diving back onto her with renewed vigor as he palmed his cock. His other hand moved up to her and he slipped one, then another finger into her.

"Yessss," she hissed as she began gyrating her hips, fucking his face, his tongue, and he loved every damn minute of it. This was the kind of education he could get behind.

He licked, nipped, sucked on the skin surrounding her folds all the while pumping his dick in his other hand. He felt himself getting close and, figuring she knew what she was talking about, thrust through his orgasm, coming all over the sheets beneath him as he continued moving his tongue, his fingers, until they were exhausted, but that was when she gasped and clamped her legs around his shoulders and he felt her inner walls squeeze around his fingers as he curved them upward and his mouth was suddenly flooded with her sweet release. He licked her clean and pulled away, realizing how sticky he was.

She chortled. "Wow. That was awesome." She glanced down at the mess on Dean and the sheets. "Looks like you need a shower."

He blushed slightly. "You said to..."

She nodded. "I sure did, baby. And that's sexy." She looked him over a moment before she sat up and fused her lips to his, pulling him onto the bed. "But first," she panted, "let's get a bit dirtier."

He smirked as she turned so he was in his back once more. He looked up at her. "Ya know, I realize I got this whole 'natural talent' thing, but I don't know if I can get it back up that fast."

She smiled. "You're fourteen years old"

"I turned fifteen almost three months ago," he growled.

She smirked. "Fine. You're practically sixteen," she said with an eye roll. "You'll be ready by the time I'm finished with you."

His eyes grew wide. "What-ah, what are you going to do to me?"

She didn't answer, only attacked. She began licking, kissing, and biting down his body. Sometimes, she left little red spots, sometimes she left teeth marks. Finally, she got down to the jizz rapidly cooling on his cock and bush and eagerly began cleaning him with her tongue, petting, teasing, until he was hard as a damn rock again. "F-F-Fuck!" he cried as she used a little more teeth. He grabbed her hair, not enough to hurt her, but enough to get her attention.

She pulled off of him and reached over to the drawer in the night stand, coming out with a condom. "Okay. Now, I know you had Sex Ed. Please tell me you at least know how to put a condom on."

He blushed again. He'd bought a couple in the bathroom of the gas station a few towns ago, and hid in the bathroom to practice with them while their dad was gone and Sammy was in bed. He'd then taken the evidence out to the dumpster afterward so Sammy wouldn't tease him about it. So he nodded. "Yeah. That one I know."

She nodded and handed him the condom. "You should be able to go a little bit longer now that you've come a few times. You'll get better at that as you practice."

He swallowed and nodded. All this stuff was awesome. But he was about to feel the real thing. She'd sucked him off, he'd gotten her off almost any way imaginable, but now it was time for the main event. Suddenly, he felt nerves like he'd never felt before. What if he wasn't good? What if he was just terrible at this? What if...

"Dean? You alright?"

He swallowed hard and nodded. Her face softened. "You can be nervous, Dean. I won't make fun of you, I swear."

"What if I suck?" he asked softly, suddenly aware of how young he sounded.

She shrugged. "Your dad and brother are gone all weekend, right?" He nodded. "My parents are, too, taking my little sister to a dance competition. So, we've got all weekend to make you a sex God, Dean Winchester. And by God, I swear we will."

He didn't even realize she knew his last name. But he smiled. "Sex God: Dean Winchester," had a nice ring to it. He ripped the condom wrapper open and slipped it on. He glanced up into her warm brown eyes. "I'm trustin ya, Tiff."

She didn't use any flowery words, didn't laugh like a villain in a Batman movie, just aligned herself with him and seated herself on his dick. He hissed as the heat enveloped him and he grasped her hips as if he knew what he was doing.

"God," she panted. "You're big."

His teeth and jaw were clenched as he started thinking about the stuff his dad had made him read about shape shifters in order to calm himself. "That's not a bad thing, is it?"

"Fuck no," she growled. She rolled her hips and he almost came. "This is amazing."

He could say the same. No description, no penthouse forum, no amount of porn could have prepared him for the awesome feeling of being buried balls deep in a woman. And it was all too evident, Tiffany might not be a Mrs. Robinson, but she wasn't just a girl, either.

She grabbed his hands and brought them to her tits. "Fucking isn't enough for some women," she stated and he wondered how she could be so damn calm as she was riding his dick, but he nodded as he tried to focus on her words. "Sometimes we need more stimulation. Play with her tits, kiss her anywhere you can reach, and..." She moved one hand down to where they were joined. "Feel free to rub her clit if you think you're not gonna last. She should always come first, at least once, if she can. Not all women are blessed with the ability to have multiple orgasms. I, however, am. So you need to make sure you get her off before you do your thing, or at the least, at the same time as you. Remember, the guy is almost always the aggressor, or certainly you will be. I can sense it." She paused. "But don't be afraid to let her lead you. You can let her take control. You might find you like that."

He nodded vehemently and she smiled as she leaned down to kiss him. "Flip us," she commanded.

He hesitated only for a moment before he grabbed her waist and, using some of the fighting skills his dad had taught him, flipped them, keeping them still connected. She gasped in surprise, but then moaned as his mouth latched on her nipple as he began thrusting slowly, mindful of the fact he didn't want to disappoint her. He was too used to hearing gruff pot shots at the many different ways he disappointed his dad on a daily basis. He didn't need to disappoint her, too. To his surprise, she praised him. "My god. Are you sure you're a virgin?"

He smirked. "Not anymore."

She smacked his butt cheek and he jumped slightly, thrusting into her hard. "Smart ass," she chided softly.

"Did you...did you just spank me?" His dad had quit spanking him years ago. Now it was usually a slap to the face if he mouthed off...occasionally something a little worse, depending on what the infraction was. Most of the time, though, John just worked him harder, made him go out into the woods, man up, quit being a little bitch, that sort of thing. It was effective.

She giggled. "I did. And you might like it if I did it again."

He might would. But that was for another day. Right now, he was feeling that pull in his gut again. It was starting. "Tiff..."

"Stop," she demanded, and he did, immediately.

"What? Did I hurt you? Shit, I..."

She shook her head. "No, you didn't. This feels great, I promise. Just...slow, go slow."

He moved his hips a few times, slow, like she said, and he felt the urge taper off slightly. She smiled. "Now, let's start building it back up again. I may not come with you inside me. Sometimes I don't. It's okay. I got mine, and that was the important thing."

Dean's eyes narrowed. If there was one thing he liked, it was a challenge. So, he smirked and bent to lick her nipple before he ran his mouth up to her ear and whispered low, dangerous, his inner hunter coming out to play. "You're coming again, sweetheart. I promise you that."

He leaned back up in time to see her eyes widen slightly, as if she finally realized, while he might be inexperienced in this area, he wasn't someone to fuck with. Hell, he killed a damn werewolf just last weekend. He dug up graves and sent ghosts packing. He had been trained to fight and kill by his Marine dad. He might be a bumbling virgin, but he was dangerous. Deadly. And he was determined as all hell to make her come again, even if he had to try and try and try, all damn night, he'd get one more her big O out of her.

He began tentatively moving again, slowly sliding in and out of her, almost all the way out, then smoothly back in, over and over, gritting his teeth as he staved off his release. He had to make her come. He had to. He looked at her face. She was enjoying it, so that was good. Hell, he was, too. Being inside of her, the warmth of her body, it was amazing. Probably the most comfortable, happiest, he'd felt since, ever. He reached a hand between them and he found that button on her body. He began rolling it between two fingers, rubbing, flicking lightly and she started to moan as her fingernails bit into the skin of his upper arms. He bend closer to her so he could kiss her again and she began sucking his tongue in earnest. He began rubbing her clit, faster and faster as he pumped harder and harder and he felt it, he couldn't stop. It was coming, but that was okay, she was too, and she let go of his tongue in time to scream out his name as her whole body seemed to convulse and he cried out as he seemed to come and come and come.

Suddenly it was like every damn moment of the day caught up with him and he had to force himself to stay upright and inside her as her body continued to quake. Finally she stilled and looked up at him.

"Well?" he managed as he panted. It felt like he'd ran a damn marathon, which he felt sure his dad would probably make him do, at least once, just to make sure he could.

She licked her lips and smiled. "I'm impressed."

He grinned.

* * *

Over twenty years later, Dean found himself riding shotgun nursing a dislocated shoulder and a headache to beat the band when Sammy flipped the radio on. Dean let out a growl but then a familiar song came on. "Love Shack" by the B-52's and Dean started humming along with it, singing the words he knew. That was the song...the song on the radio when he and Tiff were doing the deed.

"Where'd you hear that?"

Dean shut up immediately. "What?" he asked, hoping and praying Sam would just forget about this.

"I was expecting you to bitch at me for my music choices."

"Driver picks music. And judging by the fact I'm still seeing double, Sam, I can't drive. Ergo, you are driver and you pick the music."

Sam shot him the bitch face. "Jerk."

"Bitch," Dean fired back automatically.

Sam paused and then smiled. Dean returned it hesitantly. They hadn't been seeing eye to eye on much lately. But moments like this, fresh from a hunt, nursing wounds, it made it seem like the good old days.

"So? The song?"

Dean swallowed hard. "Nothing. It's nothing. Musta heard it somewhere."

Sam whipped off onto the side of the road so fast, he almost gave Dean whiplash and made his head throb even worse. "Dude! What the hell?!" Dean growled.

"You can't give a half assed answer like that without finishing it. Why in the actual hell would you even know a B-52's song?"

"Is that who they are? Chick's got a decent voice, I guess."

"Dean…" Sam's tone held nothing but warning.

He thought about lying, but they'd done so damn much of that lately. However, it was embarrassing as all hell. "Uhm, I...it was...she...hell, I don't know why I'm ashamed to admit it, but there was this girl. She taught me everything, and I do mean EVERYTHING..."

Sam's brows knit. "By everything you mean..."

"I mean I misplaced my virginity at her place." He went into detail, telling everything he could remember, which was most of it, because he had brought it to his mind almost every time he had sex. There was always something he could use Tiffany had taught him.

Sam's eyes were as big as saucers before he let out a great big belly laugh. He couldn't seem to stop laughing. "Only you, Dean!" he crowed. "Only you would manage to lose your virginity to someone who taught you everything you know!"

"Oh yeah? Well, how'd you lose yours?" Dean growled.

Sam's mouth snapped shut as he froze then blushed furiously. "It, it was, uh..."

"Lemme guess...some sweet little innocent thing? You were both virgins and bumbled your way through it, right?"

Sam didn't answer, he just winced.

Somehow, that didn't surprise him. And truthfully? Dean was glad. As fucked as their lives were, Sammy needed some normal. But he couldn't say that to Sam. That wasn't his style. So he had to tease his little brother. "Ha, I KNEW it! How bad was it?"

Sam cleared his throat and did the bitch face again. "It wasn't...terrible."

Dean snorted. "Sure it wasn't. Did you last five minutes?"

Sam didn't answer.

Dean guffawed. "Thanks, man, I'm feeling better already. Let's move our asses. I wanna find a damn bed."

"Dean...you alright? That last fight..."

Dean glared as his brother as his arm went to the mark hiding under his sleeve. "I'm fine, damn it. Now, come on, Speedy. You go fast. Drive."

Sam shot him one more look, then clearing his throat once more for effect, put the car in drive and kicked up dirt as he pulled away.

"Awww, come on, Sammy, I just washed her two days ago! Don't dirty up my baby!"

He caught Sam smiling. "Bitch," he muttered again, glad he wasn't a damn demon, and especially glad his brother was by his side.

Sam was still smiling. "Jerk," he happily replied.

Dean smiled a little, too. He didn't feel great, but he was feeling better. Maybe they were gonna beat this thing, get this mark off him. He had to keep the faith. Sam would help him research this, get this damn mark off his arm. He'd lost faith in Sam once or twice, but he was determined not to do it again.

* * *

 **An2: Was that good for you? Because I sure as hell enjoyed it.**

 **Chapter 2 will be up next week. Should be fun!**


	2. Lying Eyes

**Disclaimer: I don't own supernatural. But damn do I wish I did!**

 **A/N: here's chapter two! Sorry it's taken a while...I'm on vacation. I hope you enjoy this one, written by my lovely friend, Gina!**

 **Warnings: Smut (obviously) Verbal abuse (slightly) Lying, Cheating, I think that about covers it?**

* * *

 **Dean POV**

More than three hours into his latest conquest, Dean hits his stride again, violently thrusting. Cassandra moans loudly, "Oh...my...God! How the hell..."

"You begged and pleaded with me..." his voice drones, sending vibrations through her, "and I'm not one to disappoint." He pants as he feels himself getting close. Lowering his head to her ear he commands in a low whisper, "Now, just...ride this out with me." He changes his angle, sending her over the edge almost immediately.

She gasps, then cries out as the pressure builds. "Holy...Dean...DEAN!" As wave after wave hits her, she screams, arching her back and pressing her hips against him.

"Fuck..." he moans, biting her neck as he hits his own release. Fisting the bedsheets, he growls as they come undone together. Resting his forehead on her chest as he leans on his elbows, he catches his breath, sweat covering every square inch of their bodies.

"Whoa," Cassandra manages, limp and panting, "That was...wow."

Winded himself, Dean simply nods.

She squirms under his weight and starts giggling despite her shortness of breath.

He looks up, sweat dripping from his hair and chin. "What's so funny?" He asks breathlessly, a boyish grin on his face.

"It's nothing, really," she says, still panting. "But..." She glances upward. "Do you mind?"

"Oh...right," he breathes, smiling. Pushing off her, he sits up on his knees and leans over to one arm, then the other, untying her from the bedposts. "I'd have never guessed it, but these things are...handy," he notes. "Yeah, it's official; I've definitely acquired a silk scarf fetish." Waggling his eyebrows at her, he licks his lips. "Thanks for that, by the way." He bends down and kisses her, then collapses on his back, heaving a deep sigh. Running a hand through his sweat-soaked hair he looks at her. "Holy shit, what was that, round four? Five?"

She sits up rubbing her wrists, her hair damp and cascading down her back. "Maybe for you, but I..." she smiles as she glances over her shoulder at him. The moonlight catches her eyes, making them shimmer. "Hell, I lost count. I guess I should be thanking YOU."

He sits up and sweeps her hair over her shoulder. "My pleasure..." he brushes her skin with his mouth before giving it a bite, sending chills up her spine. Burying a hand in her hair, he turns her around and kisses her. "You're delicious," he moans, licking her lips, "but if I don't get some food, I'll be off my game...and I can't have that." He flashes a devilish grin. "Because I'm not finished with you yet. Mind if I raid your fridge?"

She chortles, "Please, knock yourself out." Kissing him again, she looks him over and says, "You've certainly earned it."

Standing up, he pulls his jeans on. "You want anything?"

As she stands, still naked and glistening with sweat, she replies, "Just bring back enough for two. I'll make up my mind then. But don't be too long, handsome..." She grabs a scarf, walks up and runs her finger slowly down his chest and stomach to his zipper, tugging. "I'm not done with you, either. And this time?" She throws the scarf around his neck and pulls him down to her for a deep, wet kiss. Pushing him back, she growls, "You're the bull."

"Yes ma'am," he says with a smirk, slapping her ass as she saunters to the bathroom. Ogling her as she closes the door behind her, he wipes his lip. "Damn," he mutters, pulling the scarf off his neck, using it to wipe sweat from his brow. He tosses it on the bed and makes his way to the kitchen, looking around in awe at the size of her house.

It's a lot for one person, but he figures that's what her kind of money affords. They hadn't gotten to know each other at all outside of first names and their mutual appreciation for hard core, two-fisted trysts, but it didn't take a genius to figure out she wasn't hurting financially. You don't sport that kind of ice for free. Actually, there wasn't anything about her that didn't scream 'well-to-do'...her clothes, what little she wore, her car, this house, her attitude...and though he found her stuffy at first, her other 'assets' were enough to make him overlook it. Besides, it wasn't her money he was after, not that he was taking advantage...she all but jumped his bones in the bar, and over the last few hours proved herself to be anything but stuffy...the things she'd done and allowed-no, begged-him to do to her...she was eagerly compliant to his every whim, and he's growing eager to respond in kind.

Thinking about it gets his motor running again, and he shakes his head. "Soon...but first, some 'left brain' fuel." He finds the fridge and opens it, revealing so much food he asks himself, "Who the hell is she feeding, China?!" Deciding it's none of his business, he starts rummaging. He opens a box of pizza, and immediately begins devouring a piece. He roots around some more and spots a bowl of fresh fruit. It's not usually his first choice, but the thoughts of it being functional as well as succulent are too tempting to pass up. He sits it out on the counter and dips his head back in to find an apple pie, then a can of whipped cream and...cinnamon syrup?

A mischievous looks spreads across his face. "For crying out loud, it's like she does her grocery shopping with sin in mind." He grabs for the golden crusted goodness when he suddenly feels the cool metal of a gun barrel pressing against the back of his neck. Closing his eyes, he freezes. "Shit."

"Don't move," a shaky voice commands.

Dropping everything, Dean raises his hands.

"Turn around. Slow."

Standing up straight, Dean slowly turns to face a visibly panicked man that currently has a revolver pointed at Dean's head. He almost mirrors Dean's height and build, but he's obviously not used to handling a gun. Dean attempts to keep him calm. He certainly doesn't want his brains blown out. "I don't want any trouble, okay? Let's talk about-"

"SHUT UP!" the man yells, his hand shaking with his finger on the trigger. Dean observes him a moment. His breathing is rapid...he's scared, which, needless to say, is...odd for an intruder. "Who the hell are you, and what are you doing here?"

Dean's brow furrows. "What am I-you're the one pointing the gun, pal! What the hell are YOU doing here?!" Looking him up and down, he notices the man's attire. "And...why are you wearing a suit and tie?" Suddenly remembering Cassandra is just down the hall, he changes tactics.

"Look," slowly reaching around, he pulls his wallet out of his back pocket as he continues to hold his other hand up. "I don't know what you want, but I don't live here, okay? I'm just...visiting." He shakes his wallet. "But there's a few hundred in here, just...take it, alright? Here, catch." He tosses it, distracting the man as he instinctively catches it. Dean seizes the opportunity to wrench the gun away before he hammers the guy with the stock, knocking him to the floor. Bending down, Dean snatches the wallet and grouses, "This is mine," before shoving it back in his pocket. Shooting an impatient glare, he motions with the gun. "Come on, get up," he orders. Standing to his feet, the man puts a hand to the gash on his left eye from Dean's blow. He hadn't hit the guy hard enough to do too much damage, just a little dent and a little blood. "All right, asshat," Dean growls, "I'm gonna give you three seconds to explain why the fuck you're here." He checks the cylinder before locking it back into place. "Then I waste you."

Dean almost felt sorry for the dude as his voice trembles. "Just...just, hold on a minute..."

Dean raises the gun, pressing it to his forehead. "One."

Unable to think straight, he stammers, "Look, I...I don't, please...let me try to..."

"Two." Dean narrows his eyes as he pulls the hammer back.

"Alright, ALRIGHT!" he pleads, holding his hands in front of him. "I-I live here, okay?! Just...just take whatever you want and go, but don't hurt my wife!"

Dean's puzzled as he looks around the gun. "Your...? Oh, hell..." Dean rubs his forehead as he realizes what a massive pile he's stepped in. "That's just...you have GOTTA be shitting me!"

Cassandra runs in, wearing a tank top and shorts, obviously to check out the commotion. The color leaves her face as her breathing hitches. "Trey." She blinks a few times. "What happened to you?!" He doesn't answer, just points at Dean. She turns to him in shock. "You HIT him?! And...why the hell do you have a gun?! PUT IT DOWN!"

"HE brought the gun, not me!" He eyes Trey cautiously. "Sorry, but I'm gonna hold on to this for now." He tucks the gun in the back of his jeans as he turns back to Cassandra, squaring his shoulders. "Well, aren't you just the manipulative little bitch?"

Still shell-shocked, she furrows her brow. "Huh?"

Dean glares. "No big deal, really...I was just grabbing a late night snack when your HUSBAND," he thunders, pointing out Trey, "puts a gun to my fucking head! Really? You're MARRIED?!" Folding his arms his brow quirks. "You wanna explain that?!"

"Oh, no..." Cassandra covers her face with her hands, as if finally absorbing the fact her one-night stand and husband are in the same room with her. She rakes her hands through her hair and whispers to herself, "What a cluster-fuck."

"Honey, are you alright? What's-what's going on?" Trey asks softly, obviously not caught up. Pointing his thumb at Dean he questions, "Who the hell IS he?!" Leering at him, barefoot with no shirt and jeans unbuttoned, he finally puts two and two together.

Dean watches Trey's expression morph from confused to anger. And boy does he look pissed off. He follows the man's eyes as they look him over, traveling from one set of teeth marks to the next. He walks over to Cassandra, lifting her head with his finger as he peruses one side of her neck, then the other, silently taking an inventory of the bruises and bites marks littering her skin. He gasps as he lifts her arms, inspecting the fresh welts circling both her wrists.

"Trey," Cassandra whispers, holding his face in her hands.

He grips her arms and forces them to her sides. As he turns around, Dean notices his eyes, brimming with tears and lit with anger. He isn't just pissed anymore...he's bloodthirsty.

Dean attempts to get a handle on the situation. He speaks calmly, "Look, I get it...you're upset, and you should be, but you gotta believe me, I didn't know..."

Trey snorts. "Upset?! I'M GONNA KILL YOU!" He lunges at Dean, ramming him into the refrigerator, landing three rocklike blows before he wraps his hand around Dean's throat.

"Trey, STOP!" Cassandra screams, trying to pull him off.

"Back off!" he yells, shoving her away. He glowers at Dean. "Who the hell do you think you are?" he grills, his tone low and dangerous. "You bring your sorry ass into MY house, have sex with MY wife?!" Something else abruptly occurs to him. He tightens his grip around Dean's throat as he rages. "In...in OUR bed?!" His jaw ticks, "Talk about a mountain of stupid...you're all kinds of screwed, Buddy, and none of the fun ways this time."

"I...I didn't know," Dean manages to choke out as he realizes he grossly underestimated Trey's strength. Dude obviously works out. A lot. He grips Trey's wrist, twisting. "You...need...to calm down." He eventually twists hard enough to loosen Trey's grip and turns him, pushing down on his shoulder as he hyperextends his arm. Trying to break his hold, Trey pushes his weight back, slamming Dean against the counter. "Fucking hell, Trey!" Dean yells, fed up and applying more pressure, "Calm down, or so help me, I'll break it!"

"NO! Dean, please!" Cassandra begs, "Don't hurt him, okay? He normally doesn't act like this..."

"Don't hurt him?!" Dean echoes, offended. "Why the hell WOULD I? All this poor bastard did was come home to find his marriage in the toilet! And if you ask me, his reaction was perfectly normal! Hurt him? You've done a bang-up job of that yourself, sweetheart!"

"Please, I just need time to-"

"Time to what?" He cuts in. "Come up with a cover story? Sorry, honey, that ship's sailed!"

"I'm not talking to you!" Cassandra snaps, furrowing her brow. "I don't explain myself to one-night heavies with an ego complex and an uncontrollable need to overcompensate. I'm talking to the man I'm MARRIED to." She takes a step forward and glares at Dean, her eyes like daggers. "Correct me if I'm wrong, but last I checked, you aren't him. So, how about you shut your pretty mouth, alright?"

He huffs. "You know what? Just stop talking."

"Why don't BOTH of you shut the fuck up?!" Trey hollers.

Dean blinks, suddenly remembering he still has his one-and-done's spouse hemmed up. "Uh, sorry. Look, you need to give me five minutes to explain myself then I'll be on my way and you two can hash this out, alright?"

"Fine," Trey grounds out through clenched teeth.

"Fine." Dean lets him go as he wipes blood from his eye and warns both of them, pointing at his back, "FYI, I still have this gun tucked away if I need it."

"Trey," Cassandra implores, "I...I'm so..."

"I swear to God, if you say 'sorry', I'm choking you next." He holds his hands behind his head, giving a self-deprecating laugh. "Seriously? I'm out of town, what, a DAY?! One day, and I come home early to find..." he motions at Dean, "some asshole in our kitchen, eating MY food after working up an appetite by screwing YOU?! 'Sorry' doesn't BEGIN to cover it!"

"It wasn't like that...I didn't mean for it to happen-"

"WHAT?!" Dean asks incredulously. "Right," he nods, "because sex happens on accident. Sure, it happens to me all the time...actually, tonight, I fucking tripped and FELL into your-"

"My God," Cassandra interjects, "do you EVER get tired of the sound of your own voice?"

Dean's mouth drops open. Snapping it shut, he pops an eyebrow. "You sure as hell don't."

She doesn't respond, just rolls her eyes. "As I was saying, Trey, I didn't plan this out. It just...happened."

Running his hands through his hair, Dean blinks in disbelief. "You shady little-that is EXACTLY what you meant to happen!"

Trey holds his arms out in exasperation. "Will SOMEONE please just explain this to me?!"

Cassandra sighs. "The truth is..." she points at Dean. "He approached me at the bar and started buying me drinks. I know I shouldn't have, but...we started drinking together and I got a little tipsy. Looking back, I suppose that was his intention all along." She pretends to will away tears as she shakes her head. "Anyway, I was in no condition to drive home, so he asked if he could drive me. I didn't have money for a cab so I agreed, and when we got here, he started..." she starts crying, "he started kissing me. I...I was drunk, I didn't know what I was doing, I swear!"

Her act is so convincing, Dean's not sure whether to be insulted or impressed, but decides to lean toward insulted. "Wow, that is...such a LOAD OF SHIT!" he roars, ready to put his hands on this spoiled little bitch himself. "You played BOTH of us, now you're trying to turn us on each other so YOU don't look responsible?! It's his fault for going out of town, my fault for being in the bar...where exactly does your fault lie in all of this?"

Cassandra immediately loses the crocodile tears. "MY fault?!" She points at herself, then at Dean. Looking up, she pretends to think as she adds on her fingers. She nods, "Yeah, just like I thought...it definitely takes TWO people to do what we just did, so save that self-righteous attitude for someone you didn't just hit the sheets with! Besides, YOU hit on ME, remember?!"

Dean guffaws. "You are GUANO, lady! If memory serves, the flirting went BOTH ways, and I remember you practically DRAGGED my ass here!"

She puts a finger to her chin. "You know, what I DON'T remember are complaints or protests!" she screams.

"Same goes, sister!" Dean fires back. "Truth is, not only were you NOT complaining, you were BEGGING, itching to be strung up and exploited six ways from Sunday, and I DON'T mean that figuratively!"

"Really? And who was at the business end of the strings? Oh, that's right, it was YOU!"

"HELLO!" Trey bellows. "I'm standing! Right! Here! I can literally hear every word!"

"Dean, please," Cassandra pleads, softening her tone, "don't you think you've caused enough trouble?"

"I'VE caused trouble?!" Dean's emotional state goes from anger to outrage like flipping a switch. "I have NO problem taking my part of the responsibility in this, but I will be DAMNED if you're gonna paint me as some kind of fucking creep who forced you into something you didn't want, and I'm sure as hell no home wrecker, Cassandra! YOU'RE the one who walked into that bar with the full knowledge that you belonged to another man...had I known?" He looks at Trey sincerely. "Had I known, I swear to God, I would have sent her packing."

"Just...go. I need to talk to my husband and your being here isn't helping." Cassandra says, attempting at being anything but a cold she-devil.

"No, YOU being here is the problem!" He sucks in a breath. "Do you realize what happened here before you walked in?" Trying to make her understand the gravity of the situation, he explains. "He had a gun on me, trying to protect you. I took it away and pointed it at HIM, trying to protect you. We nearly KILLED each other, trying to protect YOU, when the truth is, if it weren't for YOU, none of us would even BE here!" Shaking his head, still resisting the urge to choke her to death, he turns to Trey. "I know we don't know each other and this isn't the ideal way to make intros..."

"No shit," Trey growls.

Dean shrugs. "I sure as hell don't expect you to believe a word that comes out of my mouth. I wouldn't in your shoes. But if you want the truth, the REAL truth..." He motions toward Cassandra, "Trust me, you ain't gonna get it from her."

"Trey?" Cassandra asks, holding her hands out to him.

Sighing, he looks at Dean. "Talk."

"WHAT?!" Cassandra shrieks. "You're gonna believe some stranger over your own WIFE?!"

"What do you expect me to do?!" Trey yells. "I came home, expecting to find my wife, but instead I find my wife, AND her current piece of ass! Now, regardless who picked up who, he sure as shit didn't get in here without a key! And you still slept with him, so no matter what, at the very LEAST, you've proven to be a..." Looking to Dean for help he asks, "What'd you call her?"

"A manipulative bitch?" Dean offered.

"Right, a manipulative bitch! So if you don't mind, I'd like to hear from the one person in this room who has nothing to lose by telling the truth!"

"Thanks..." Dean rubs his hands together, trying to find the right words. "Alright. I, uh...shit, I need a beer." Looking at Trey, he points at the fridge. "Do you mind?"

Trey scrubs his hands over his face. "Go ahead." He walks to the table and grabs a couple of chairs, bringing them over by the island. "Grab me one?" he asks, taking off his jacket. He opens the top button of his shirt and loosens his tie, pulling it over his head. He tosses it on the counter and rolls up his sleeves as he sits down.

"Sure." Dean snags a couple of beers, tossing one to Trey. Twisting the top off his, he throws it in the sink as he seats himself across from him. Buying himself some time, he turns it up, nearly downing the whole thing. Finally pulling the bottle from his mouth he breathes out, "I should probably preface all of this by saying that tact and subtlety? Not my thing, so I apologize in advance for sounding...harsh."

Trey takes a long drink himself. He wipes his mouth before replying, "I was present for the screaming match just now, remember?" Dean winces. "The PSA would've been a little more helpful prior to THAT. Now?" He shakes his head as he presses his beer to the cut on his eye. "Not so much, but noted." Leaning an elbow on his thigh he shrugs. "Well?"

"Okay, so..."

"Press pause," Trey says, holding a hand up, slamming his beer down on the counter. Spotting Cassandra trying to make an exit, he walks over and grabs her by the wrist, then gets another chair. Hurling it down next to his, he pushes her onto it. "Don't. Move," he warns. Looking at Dean as he takes his seat again he says, "Continue."

Dean blinks. "Okay. You wanna know if I picked her up at the bar? Yeah, I did..."

"See?! I TOLD you!" Cassandra exclaims.

"BUT..." Dean says, pointing a finger at her, "she's the one who walked over to me, dressed like sex on heels and coming on like some drunken prom date."

"Hey!" she yells, "You sure as hell didn't have a problem with it, buying me drinks, telling me on the one-to-ten scale I was a 'holy shit'!"

As Trey looks back at Dean, he rubs the back of his neck nervously. "Shit...sorry," is all he can offer with a shrug. Then he counters, "First of all, she hasn't denied ANYTHING I just said. Second, she said I came to the bar hitting on HER?! I don't wanna call her a liar, but...she's a fucking liar. I was already there, had been for a couple of hours, feel free to check with the bartender. In my opinion, though, the question you should be asking is this; regardless of who hit on the other, why was she there AT ALL?!"

Trey glares at Cassandra now. "Well? Do you have ANYTHING to say?"

"Trey, come on, don't tell me you actually BELIEVE him! He's-"

"Why don't you hold that thought, sweetheart?" Dean stands up and says, "just...give me a second." He disappears to the bedroom, reappearing moments later with Cassandra's clothes. Dropping them in front of Trey he says, "By all means, you don't wanna believe me? Fine." Directing his attention to her clothes he says, "This is what she was wearing. Wanna know what she WASN'T wearing?" He reaches out and grabs her left wrist, holding it up and pointing. "Her wedding ring. She was wearing bling all over...earrings, necklace, bracelet, but I never saw a damn ring on EITHER hand. Trust me, I'm no amateur, it's the first thing I look for. And in case you didn't notice, she STILL hasn't bothered to put it on." Cassandra growls as she jerks her hand away.

Trey reaches down, sorting through her clothes. Looking at her he whispers, "Why have I never seen any of this?" Cassandra doesn't respond, just turns her head, staring a hole in the wall.

"Okay," Trey contemplates, "you didn't know at the bar. But how in the hell did you miss it when you got HERE?!"

Dean sits again, pondering the question. He scrubs a hand over his mouth, trying to recall something, anything. Then it hits him why he can't. "Come with me," he says, walking to the front door, Trey following behind. Turning around at the door Dean says, "Look...what do you see? There isn't anything here...not a picture, a magazine, a pair of shoes, NOTHING to suggest she might be married, much less that a man has ever LIVED here." They go through the rest of the house, room by room, and it's all the same.

Trey leans back against the wall, fisting his hair. "What the hell?! It's...it's like I don't even KNOW her!"

"Honestly?" Dean winces. "I'd bet money she's no amateur either. I mean, this..." he looks around, "this is downright methodical. She's been playing you, man...for a long time."

Staring off in thought, Trey questions Dean again. "How..." he swallows hard, "how long have you been here?"

Dean shakes his head and grimaces. "Come on, don't do this..."

Trey steps in Dean's face, shoving him. "I'm her husband, dammit, I've got a right to know..."

"Why does it matter? It won't change any-"

"HOW LONG?!"

Dean looks at his watch. "Before you got here?" He looks at him apologetically and responds, "At least half the night."

Trey scrubs a hand over his mouth. "And you've been...with her? The whole time?"

Dean hangs his head.

"ANSWER. ME."

Dean nods, looking him in the eye. "Yeah. Till you found me in the kitchen."

"That damned lying..." He punches a hole in the wall, making Dean jump.

"Whoa, man! Calm down-"

He punches another hole, then storms back to the kitchen clenching his teeth.

"Shit," Dean mutters, following after him. He doesn't want to involve himself any more than he already is, but he can't let Trey so something stupid either.

Just as he breaches the door he sees Trey take Cassandra by the arm. Jerking her from the chair, he growls, "Get out," then slings her toward the door.

"What?! Trey, where am I supposed to go?"

"I don't know, why don't you head back to the bar? I'm sure someone there will be more than happy to take you! Either way, I'm not troubling myself over it. We're done."

"Trey, please don't do this...think about what you're saying!"

"Oh," he pauses, "wait." Turning around he grabs her clothes and shoes off the floor. "I thought about it...here," he says, flinging them at her, "don't forget to dress for the job!"

"Baby..." she starts crying. "Please. I'm so sorry. Forgive me, PLEASE."

He doesn't even attempt to argue, just points at the door. "Go."

Seeing she's past the point of getting back on his good side, she turns off the water works. "Fine," she seethes, "but I'm not leaving here without my things."

"Really?" He gets in her face, backing her against the wall. "Cause I'm betting you will. Tell me, what in the hell is here that belongs to you? I bought and paid for EVERYTHING! Just like I've always done, like I would've continued to do! Since I met you, all I've done is bend over backwards to make you happy! And what do I get for my trouble?!" He's almost trembling as he roars, "A GODDAMNED reach-around!" Cassandra jumps at his tone. "All you had to do was enjoy and NOT be a fork-tongued whore!" He clenches his fists, then sucks a breath through his nose. "Since I'm a nice guy though, I'll see to it you get your things, but not right now. Right now, it's time to go."

"You can't just toss me out on the street!"

"Why not? Isn't that your stomping ground?! Get. Out. NOW!"

She doesn't say another word, just heads to the door, slamming it behind her so hard it shatters the glass in the window.

Dean's been hanging back, awkwardly watching things play out. Deciding he's done enough he clears his throat and says, "So, I guess I'm just gonna..."

"Yeah," Trey replies tiredly. "That's probably a good idea."

Dean heads to the bedroom and finishes getting dressed. Passing Trey as he heads out he stops. He takes a breath. "For what it's worth, I'm sorry. For everything."

Trey groans. "It's okay."

Dean's eyebrows shoot up. "Seriously. Just like that?"

He sighs and rubs the back of his neck. "I mean, what can you do, right? Though, I gotta admit...getting to crack you in the face a few times?" A self-satisfied smile spreads across his face. "That was pretty damned sweet."

Dean manages a chuckle. "Glad I could help. He shrugs and adds, "Same goes, I guess."

Trey shakes his head. "She screwed us both, no pun intended...or would it be every pun in this case?" He snorts, "Anyway, I figure, if it hadn't been you, it would've been some other guy, but he wouldn't have cared." He steps forward and holds out his hand, looking him in the eye. "You're alright, Dean."

There are few times in Dean's life that complete strangers just blow him away. This is one of them. He grips Trey's hand and shakes it as he says, "Thanks, Trey...really. You too." Holding up a finger he says, "Oh, I almost forgot..." reaching behind him, he pulls out the revolver. "This is yours. If she comes back, you might need it." As Trey takes it he looks at him a minute. "This might sound crazy, but.." he points his thumb at the door, "wanna grab a drink?"

Trey chuckles flatly as he tosses the gun on the sofa. "Yeah, I could definitely use a few of those, but only if you're buying."

"It's the least I can do after everything that's happened." As he turns to the door Trey stops him. "Wait, I've got an idea. C'mon." Dean follows him back to the kitchen. He reaches into a cabinet, grabbing a bottle of scotch and a couple glasses. "How about," he says as he pours, "we stay here," he hands Dean a glass, "and you help me pack her shit?"

Dean holds his glass, thinking. He points over the top of it. "By 'pack her shit', you mean..."

"Get drunk, take her stuff and use it to litter the back forty."

Dean tosses back the scotch. "Wow, this is good..."

"I don't bust my ass for the cheap stuff," Trey remarks. "Ready for another?"

Dean hands his glass over. "Absolutely." It only takes him a second to decide the idea of getting revenge on Cassandra is almost as good as the scotch. Both are even better. Nodding, he responds, "Hell, I'm game, let's do it. Where is this 'back forty'?"

"The in-laws' country club." Dean shoots Trey a look. Shrugging he says, "Maybe you're right, that's not be the best idea." After taking a shot he says, "Let's just make a pile out back, strike a fucking match and call it a day."

"Sounds like a plan," Dean says. He looks off in thought. "You got any salt?"

"Yeah," Trey answers, confused. "Why?"

"Just...trust me, you can't be too careful."

* * *

The sun is rising when Dean finally walks into his and Sammy's motel room.

"Hey, I was about to put out an APB on your ass," Sam chuckles as he rubs the towel over his wet hair. From the looks of him, he'd just come from the shower after his morning run. "Where you been?"

Dean just looks at his brother. "Sammy, after the night I've had, trust me when I say, you don't want to know."

Sam's nose curls. "Please. Do not give me any sex details."

Dean just shakes his head as he thinks about the night he's just had. "You wouldn't believe me if I did tell ya."

Sam's brows furrow as he sees the bruises forming on Dean's face. "You okay, man?"

Dean just smiles. "Never better. Now, I need a hot shower. Did ya use it all up jacking off in there to thoughts of Britney Spears or some shit?"

"Jerk."

"Bitch," Dean snarls, but he's smiling as he says it.


	3. Redhead Walking

**disclaimer: uh...I don't know, man, I don't own it. I only own a warped mind. Don't sue me, okay?**

 **Author's Note: okay, so, this ones been dogging me ever since I first watched 9x02. I'm sure everyone has written a Dean/Abaddon fic, but I haven't found one to read, so, maybe I'm the only one with a warped mind? Anyhow, this is a sort of scene insert into that episode. I may expand on it in the future, maybe to the 9x22 episode where Dean kills her, but I don't know yet. We'll have to see. This is a collection of Dean sex scenes, so there is no order, just what I feel like writing or what Gina feels like writing. Hope you enjoy!**

Dean/Abaddon

I Got a Thing For Gingers

He knew, looking up into her eyes, he knew how this was gonna go. And he couldn't help but mouth off as he asked, "Are we gonna talk, or make out? 'Cause I'm getting some pretty mixed signals..."

Her eyes narrowed as she brought him closer. "Both," she growled as she forced her lips to his.

He tried to move away, but the demon's grip was too strong. There was no way he was going to fight this off. He'd been there before, forced by a demon to...

"I won't do that," she purred softly.

His eyes opened wide. "D-do what?"

"Take you without you wanting it."

He gasped, wondering how she knew. Alastair was dead. No one should have known... "Ain't that kind of what you're doing now?" he managed.

She shook her head. "No. Because you want this body. You want me."

"And the poor chick you're riding? Josie? What's she want?"

Abaddon laughed. "She wanted Henry. His grandson will do just fine."

"No. I'm not raping that poor girl just so we can get our rocks off!"

She sneered. "I knew you wanted me." Her face softened, "No matter. Josie died, a while ago now. It's just me hanging out in this meat suit."

"You swear it?"

She eyed him oddly. "You'd trust the word of a demon?"

Dean attempted to shrug. "You said you wanted me, you wouldn't force me. I'm inclined to believe ya. And I believe ya about this."

Her head tilted to the side, contemplating him. "Why?"

"Because. You're a lot of things. A manipulative bitch is at the top. But you're not a liar. Demons lie, yeah, but not you. You don't gain anything by lying to me."

She smiled again. "What is it about you, Dean Winchester?"

This time he smirked at her. "Hell if I know. But you want me, and I been getting a hard on for that meat suit of yours almost since day one."

Now it was her turn to question. "Why?"

"I got a thing for gingers."

That was she needed as she molded her mouth to his and by God, it felt good. He hadn't been laid in forever, and he needed the release. And this demon chick was gonna help him with that. He thought about how wrong this was. How he'd raked Sam over the coals for doing Ruby. But this...there was no subterfuge, no ulterior motives, just two creatures in need of a good fucking.

He moved his hand to touch her and she let out a snarl as she flipped him onto his back and pinned him with her powers. He looked up at her as she pulled off her leather jacket. He tried to move, but he was frozen in place. She smiled. "I rather like you at my mercy."

His eyes widened just a bit. "You...you aren't going to kill me, are you?"

She smirked. "Not today."

He managed to nod before she knelt over him and undid the button on his jeans.

"Where's Sam?" he asked before she could snake her hand inside.

She pulled her hand away and shook her head. "I will not let my minions kill him either."

"You swear it?"

"On the name of my lord."

He sneered. "Lucifer's name doesn't mean much to me."

"No, but it does to me."

He eyed her a moment. Maybe it was the fact his dick was as hard as a diamond and he needed to get his rocks off. Maybe he saw something in her no one else had. Or maybe he was just a damn glutton for punishment, but he breathed, "Okay."

That was all the encouragement she needed as she grabbed his cock and he groaned when she pulled and squeezed. "Fuck," he growled.

She smirked. "Just give me time, baby. I'll do thing to you that will make you question your sanity."

"Pretty sure I'm already doing that," he hissed through clenched teeth as he felt his pants being tugged down, exposing him to her. He felt the dirt and scattered rocks under his ass, but then she pulled her shirt off and he honestly didn't give a fuck as his eyes grew wide.

She smirked as she slithered out of her pants as well and he was speechless. Her body (because he damn sure didn't want to think of it as a meat suit at the moment,) was sexy as all hell, and all that damn red hair...those eyes, green like his, pierced him. "See something you like?"

He couldn't help the grin. "What do you think?" He moved his hips just slightly and was glad he could. His arms were still pinned down, but his pelvic region was gloriously free. He wiggled it a little bit for effect and enjoyed watching her eyes grow wider as he twitched his cock at her.

She let out something like a cross between a snarl and a scream as she pounced, kissing, biting, sucking and he could do nothing but hold on as she all but worshiped his body with her lips. He felt her teeth on his nipple and he almost came just from the sheer pleasure/pain she was inflicting. "Need...fuck, I need more," he whimpered.

"You mean this?" she hissed as she teased him, dipping her pussy to touch him.

He bucked his hips, but she ignored him as she continued her slow torture of him. "You are so delicious, Dean. Oh, the things I could do to you..."

"You gonna keep yapping or you gonna fuck me?"

Her eyes narrowed and she scratched those blood red nails down his chest, cutting him in the process and he cried out in pain before he groaned in pleasure as she sank onto him. "Like this, lover?"

His eyes rolled back in his head as she began rolling her hips, riding him for all she was worth and he could do nothing but enjoy the sensations flowing through him.

He lost all sense of time as she moved, getting her pleasure, denying him his. Of course, he was still enjoying the hell out of it. She was riding out her fifth orgasm when he felt his coming. "I'm-I'm..."

"Come," she commanded and he was powerless as wave after wave of pleasure flowed through him.

He panted out a breath as she stood and began to dress. He felt her powers leave him and he was free to stand. He slipped his jeans back up his hips and straightened his shirts. He cleared his throat. "So...uh..."

She glared at him. Now that they'd done the deed, apparently they were back to being enemies. That was good. Enemies he could handle. "I want Crowley. Or what's left of him."

He eyed her. "Yeah? What's in it for me?"

"I let you die. You give me Crowley's head, and I will snap your neck, quick and clean. You won't feel a thing, trust me."

So...they were back to hard balling already, huh? "And if I tell you to get bent?"

She sidled up to him, clothed once more, and grabbed him by the shirt. "Oh. Well... you know, I've loved this body since the moment I first saw it. You're the perfect vessel, Dean. You give a girl all sorts of nasty ideas. So go ahead and play hard to get, and I'll peel off this "no demons allowed" tattoo and blow smoke up your ass."

She could. He'd seen Crowley do that very thing to Mrs. Tran. And yet, he couldn't keep his trap shut as he told her, "Oh, well, I gotta tell you, between you and me, it is a horrow show up there."

"It can get worse. Trust me. 'Cause once I'm on top, I'll make you watch. And I'll use your body. Have you ever felt an infant's blood drip down your chin? Or listened to a girl scream as you rip her guts out? Because you will. You and me, lover. We'll have a grand old time."

His eyes narrowed and he pushed her away. "You think you're being cute, Abaddon, but you're really just starting to piss me off."

"You're an insignificant human, Dean."

His eyebrow rose. "Yeah, but I'm one you can't seem to stop wanting."

She grabbed him again and once more he felt himself being forced to his knees. "I could do such terrible, depraved things to you, Dean..."

"But you're not gonna. Not yet, anyway."

"Give me what I want!" she demanded, an almost childish plea in her voice.

He shrugged. "Right now, Crowley's the lesser of two evils, babe. So I gotta throw my lot in with him."

Just then, there was a bright flash of white light from within the diner, blasting out all the windows.

Abaddon glared at him. "An angel?!" she screeched.

Dean's smirk filled his face. He was assuming Zeke had done his thing and came out in Sam, as creepy as that thought was. "What, you think we'd roll up to this mouse trap without some backup?"

Abaddon grabbed him by the throat and threw him aside before she disappeared.

Dean panted out a breath and ran toward the diner. He'd think about everything that had just transpired, later. Right now, he had to check on his brother.


	4. I Hate My Life

**Disclaimer: I do not own Supernatural. But if I did, I'd get Misha a bodyguard so he doesn't get attacked again!**

 **AN: Hi, all! Here's the next chapter in the Sexcapades of Squirrel. This one was co-written by Gina and I. All the stuff with Jordan is hers, mine is the before and after. LOL. And the song is by Theory of a Deadman. The fic is loosely based on it, if that gives you any hints! Hope you all enjoy!**

 **Warnings: None that I'm aware of. Cursing, smut, alcohol, that's about it.**

* * *

 **I Hate My Life – A Sexcapades of Squirrel Story**

Dean's eyes narrowed as he walked past the guy begging for change. He dropped a buck in, because, hey, shit happened to people. He noticed Sam dropped a couple of bucks in as well as they walked back to the Impala. "You know, some days, I wish that was us," Dean stated as he looked over the roof of the car at his brother.

"Begging on a street corner?!" Sam asked indignantly.

"Yeah. Beats the hell out of this life sometimes," Dean muttered as he slipped in behind the wheel. Sam blew out a breath as he slid into the passenger seat. "What?"

Sam shook his head.

"Don't do that. You got a problem? Say it."

"Dean, that guy...he's living on the street for crying out loud!"

"Yeah? So? No monsters to hunt, no death tattoo on his arm..."

Sam's eyes cut to Dean's cloth covered arm where The Mark of Cain was perched and Dean sighed. "All I'm saying? He sits on a fucking street corner. That's it. He may be homeless, but he's got a hell of a lot less complicated life than we do."

"You're acting like an ungrateful brat."

Dean glared at him. "And you're bitching at me like you're my wife, Sam! Geez! If I can't bitch and whine to you, who can I?"

Sam rubbed his eyes with his middle finger and thumb. "I'm just saying, we could have it a lot worse."

"I was a demon, Sam. You were Lucifer. Explain to me how much worse our lives can get?!"

Sam shot him the bitchface. "You know what? Forget homicidal, that damn mark is turning you into a whiny bitch!"

"You're the bitch, bitch."

Sam sighed again and rolled his eyes. "Look, let's just..." he sucked in a breath then blew it out. "Look, I'm glad you're attempting to clean up your life a little bit, and I'm glad you're not drinking as much, but, damn it, I think you need to get a drink. Drop me off at the motel, let me do the research. Go get plowed, get laid, and come back in the morning with a better fucking attitude, okay?"

Dean blinked. "You..." He thought a moment. That...didn't sound like a bad idea. "Fine," he bit out, almost grateful for Sam's suggestion. "I'll do that."

"Good."

They didn't speak until Sam got out of the car. He leaned back in and glared at Dean. "I mean it. Don't come back until you're lit and laid."

"Thanks, you're so fucking kind," Dean growled. Sam slammed the door and Dean tore ass out of the parking lot, squealing tires as he went.

He drove to the nearest bar and walked in. It wasn't a dive, it was actually a fairly decent place, complete with a bouncer at the door, checking I.D.'s. Dean sauntered up to the bar and plopped his ass on a bar stool.

"What ya have?" the bartender asked.

Dean ordered a beer, just to get him started, along with a shot of whiskey. He downed the shot, and took a sip of the beer before he looked around. His eyes zeroed in on an ass that wouldn't quit wrapped in denim so tight, he didn't know how she was breathing, but it was working for her. She had on too much makeup, and she was laughing a little too hard at some other chick's joke, but he shrugged and leaned over. "What's so funny?" he asked her.

She turned and gave him a dazzling, toothy grin. "Inside joke between my girl over there and me." She held out a dainty hand. "Jordan."

"Dean."

She looked him up and down and he didn't need Sam's college education to know she was sizing him up. He cleared his throat. "My eyes are up here, honey."

Her grin grew as she licked her lips. "Yeah, but..." she slid closer to him and her hand hit his thigh, then kept going, right up to little Dean, who was growing by the damn second. "No matter how pretty they are, this is what I'm interested in."

His eyebrow shot up. "Direct, huh? I like that. Wanna get out of here?"

"Sure," she purred as she leaned in to kiss him. It started off soft at first, but then she nearly devoured him as she threw her arms around his neck.

He couldn't help the moan as he managed to shove his hands into the back pockets of those jeans, squeezing her ass as she fisted a hand in his hair, tugging a little rougher than he liked.

Suddenly, she was pulled from his arms and a guy about Dean's height and build yelled, "Say goodnight, Jordan!"

"H-Hey!" she shouted as he pulled her roughly toward the door.

Dean instinctively grasped her around the waist, pulling her back to him. "The hell's your problem, pal?" he growled, guarding her as he stepped between the guy and Jordan.

The man looked around Dean to stare Jordan in the eye. "She's leaving. Now!"

"Sorry, bud, you're gonna have to do better than that," Dean stated arrogantly. "She may not have come with me, but she's here with me now, and guess what? She's planning on leaving with me. So, just go on. She's not interested. Go on back home. Unless you wanna try me. Think you could throw me outta here? Be my guest."

The guy narrowed his eyes and stepped so close to Dean, they were almost touching noses. The guy's tone was nothing but dangerous as he growled through clenched teeth; "Well, as her FATHER, trust me when I say it'll be my absolute PLEASURE to kick your ass out of here."

Dean blinked, frozen. The man looked him up and down. "You're still standing between me and my daughter, who happens to be SEVENTEEN, jerkoff. You wanna move? Or are you going to make me put your lights out, first?"

Dean knew a bluff when he saw it, and this was not one. He cleared his throat. He swallowed hard. "No sir," he whispered as he stepped aside. "Sorry."

They guy was still eyeing him as he snatched at Jordan, who pulled Dean in for another searing kiss.

"Young lady, you're in enough trouble already!" her father yelled at her, tugging her away.

She slipped something into Dean's hand. "Call me!" she yelled before sending him a wicked smirk and a wink.

Wide eyed, Dean glanced down at his hand where a phone number was written on a napkin.

He staggered back to his stool and fell onto it. With a sigh and a head shake, he muttered, "Fuck my life."

* * *

The next night found him sitting on the same barstool. They'd ganked the monster, saved a civilian, and were big damn heroes. Sam was going back to take a shower, but Dean just needed a little something to take the edge off. After not managing to get laid the night before, coupled with almost feeding some teenager's daddy fetish, he just needed to regroup. He'd gone back to the motel shell-shocked, prompting Sam to look at him worriedly. Well, at least he hadn't murdered anyone, right? That had to count as a damn win. Didn't it?

He ordered a beer along with a couple of shots and was lining them up to drink when he heard a voice purr from behind him, "Hey, you."

Wide eyed, he turned around slowly. Sure enough, it was Jordan, wearing a red dress that fit her like it should be thanking her. His eyebrow shot up. "NO."

"What?" she pouted playfully as she wrapped a lock of hair around her finger, twirling it innocently.

He shook a finger at her. "NAH-uh. Keep movin', Juno. The last thing I need is to star in my own episode of 'Teen Mom'."

She laughed throatily and wrapped an arm around his neck, fingering his hairline lightly as she got into his personal space. She ran a finger down his chest and with a flirty smile, said, "Now, Dean, are you trying to tell me you didn't have fun last night?" Dean stood stock still. Her smile grew predatory as she pushed into him. "Are you trying to say you don't want to take this out for a spin?" She put his hand on her hip. "Trust me, I know what I'm doing. I know how to treat you right, Daddy."

He held up both hands like she had a gun on him. She put a hand on his face and breathed, "I promise, I can make you feel so good."

Dean closed his eyes and muttered to himself, "There's no pie in jail, there's no pie in jail, there's no pie in jail..."

He grabbed both her wrists, forcing her hands to her sides. "First of all," he looked her up and down, unable to help himself. "DAMN. That dress is sin."

With a smile, she began to lean in again.

"No. STAY!" he commanded. He shook his head, trying to rid himself of the mental imagery. And it was oh...so...inventive. "Second of all, if the 'fun' you're referring to is that standoff I had with your old man? Yeah, that was LOADS of fun. Thanks. Can't wait to do it again."

"I didn't peg you as the type to back down from a challenge so easily," she stated with a playful smirk.

He shot her a look. "No way in hell I'm biting THAT hook. A challenge I can handle, trust me, but not one that tacks on five-to-ten." He stared off in thought a moment before looking back at her. "Seriously, how did you even get in here?"

She moved a step closer as she said, "Let's just say the guy working the door doesn't play hard-to-get nearly as well as you do."

"Wow," he stated, feeling a mixture of surprise and pity. He glanced at the dress again. "Red's definitely your color, 'cause you're the devil. And trust me, that's not a compliment. I've met the bastard." At her confused look, he pushed her away with a single fingertip to her shoulder so his intentions couldn't be misread. "And FYI, that information just earned the douchebag at the door a beatdown, not to mention a cell mate named Bubba. Hope he likes it rough..."

For the first time, her composure slipped as she whined, "What?! You can't do that!"

He smiled, feeling back on his game. "Sure I can. It's one of the privileges of being a grown-up." Downing one of the whiskeys behind him, he added, "Consider it an apology to your old man."

"I'll never be able to get in here again!"

He leaned back on one elbow. "And that's a bad thing?"

She just looked at him, wide eyed, mouth all but hanging open, speechless.

He turned and asked the bartender, "Buddy! Can you call a cab? I'm pretty sure I'm about five seconds from a meltdown here."

The bartender nodded and Dean turned back to the girl as she screamed, "You...YOU ASSHOLE!" She stomped her foot. "I'm not a kid, and not you, not my dad, NO ONE is gonna tell me what to do!"

He finished his beer then got to his feet. "See? THAT'S how a teenager's supposed to act." He grasped her arm and began moving.

"What the hell do you think you're doing?!"

"You're going home. It's past your bedtime."

"Like hell!" she spat as she pulled her arm away from him. "You may be as old as my dad, but you ain't him, so let. Me. GO!"

"HEY!" he barked. He started to argue but instead, popped an eyebrow. "I may not be Bieber or whoever, but it sure as hell worked for you."

Her mouth fell open. "Oh! You mother..." she slapped his face. Hard.

"Ow, dammit!" he growled, rubbing his cheek. She moved to swing again and he grabbed her wrist. He leaned in close and warned, "Don't let this pretty face fool you, honey. I ain't above carrying you outta here unconscious if I have to. So? You done yet?"

She jerked her wrist out of his hand and squared her shoulders. "Jerk," she muttered.

Like a reflex, Dean shot back, "Bi-ahhh..." He winced and rubbed the back of his neck.

Her eyes narrowed. "What did you just say?!"

He cleared his throat. "Never mind. Let's go."

Surprisingly, she let him lead her to the door. As they approached the bouncer, Dean pointed at the girl next to him. "You know her?"

The bouncer chuckled nervously. "So many girls are in and out of here, man, it's hard to keep track, you know?"

Dean had been trained in reading bullshit since he was a child and he read the recognition in the guy's eyes immediately. "Yeah, I bet," Dean murmured. They moved through the door and Dean threw an elbow into the guy's face, knocking him against the wall. The bouncer slid down to the floor, clearly unconscious. With a sneer down at the body, Dean stated, "Don't move. I'll be right back to finish this."

Dean was surprised to find the cab already waiting outside. He opened the back door and shoved Jordan into it. Squatting down, he pointed at her. "Don't think I won't find out if you end up anywhere but home."

"Whatever, Grandpa," Jordan replied, crossing her arms.

"You're welcome, by the way," Dean growled as he slammed the door. He walked around to the driver's window. He leaned in and waved a fifty in the driver's face. "See this? TAKE. HER. HOME. Don't pass go, don't...well, you know the rest."

"You got it," the driver said, dropping the money into his shirt pocket.

Dean took a step back as he watched the cab pull away. He scrubbed his hand over his face and groaned, "Holy shit. What a night."

He walked back into the bar and moaned as he saw the bouncer, still out of it. "Hell, I'll deal with you later," he sighed, swatting his hand in the idiot's direction. He stepped over the body and plopped back down at his seat. He looked at where the shot glasses had been lined up. Apparently the bartender hadn't figured he was coming back. "Damn." he waved a hand at the bartender and pleaded, "Whiskey. Double."

He heard a feminine giggle coming beside him. He downed the drink and glanced over. She was wearing jeans that fit her just right and a top that showed off cleavage you could die happy in. The woman smiled at him.

"Well, hello there," he stated with a smile to match.

She leaned into him and whispered, "You look like you could use a little company."

He opened his mouth to accept her offer before he remembered the night's event's thus far. "Wait...are you over twenty-one?"

Laughing throatily, she replied, "Wow. You flatter me. Yeah, I am. And then some." She looked him up and down. "I'm probably older than you are, gorgeous."

He flashed her a boyish grin. "Is that so? Well then, by all means, let me buy you a drink."

* * *

They sat and talked a while. She was flirty, fun, sexy...he needed in her pants. So by the time the bar closed, and she purred, "Let's get out of here," into his ear, he was all too willing to comply.

He followed her back to her car and slid into the passenger seat, to let her run the show. She tried to give him the whole 'I don't normally do this kind of thing' line and he half bought it until she pulled up at the motel he and Sam were staying in. She smiled and said, "I think we should get a room, don't you?"

How could he argue? He could cut glass with his dick. He needed this. Now. But he didn't want to appear too eager. "Sure, sugar. Want me to...?"

She shook her head and winked. "I got this."

He watched her walk in and he whimpered before sending Sam a text; "About to be a very happy boy, Sammy. See you when I see you."

Sam sent a green faced sick emoji and Dean chuckled. It was followed by the comment, "Stay safe."

Dean rolled his eyes. Like he didn't know how to stay safe. He snorted and sent back, "I've got my angel blade."

This time Sam just sent back a colon and a capital P - two eyes with a tongue sticking out. Dean was still chortling when she came back. "Something funny?" she asked.

He shook his head. "I just wanted to check in with my brother. He worries."

She eyed him but didn't comment as she drove and parked a few parking spaces down from the Impala. He glanced at his baby before he followed the woman into the room. "You know," he stated as he broached the door, "I usually make it a point to know the names of the women I'm having sex with."

She sidled up to him. "What do you want it to be?"

He shot her a deadpan look. "Okay, listen, I've been burned before. I don't do cash for ass, you feel me?"

She gave him that throaty laugh again and tossed her hair. "No cash, just...anonymity."

"You got a mob husband or something?"

"Or...something."

"You're not married, are you?"

Again, with the laugh. "No. I just have a reputation that doesn't lead to having a late night rendezvous with a stranger."

He nodded. "Fine. No names. I'm cool with that."

"Really?"

He gave her a soft smile and put his hands on her hips, pulling her to him. "Sugar, sweetheart, cupcake, I can call you all the names you want."

"Sounds like a plan to me," she whispered only a moment before her tongue snaked into his ear. "Let's get naked."

She gave him a push and he landed on the bed, propped up on his elbows. His mouth ran dry as she pulled her shirt over her head, revealing those glorious tits to him. "Fuck, you're beautiful," he murmured as she straddled his waist.

She smirked and bent down to take his mouth, and take she did. She definitely knew what she was doing, and she did things with that mouth that made him question his sanity. This was just what he needed.

She unbuttoned his shirt at lightening speed and bit as his chest as she moved down, down down, "HOLY FUCK!" he cried as she deep-throated him. When did she unfasten his pants?! He felt her hand on his and she moved it to her head. His eyebrow popped. _Dirty girl likes it rough. Okay. I can work with that..._

He fucked her mouth and she took him like a champ as he continued thrusting. She nipped, sucked, tongued, he'd never had his cock and balls worshiped quite as thoroughly as she did. Finally, when he was almost at his breaking point, she pulled away.

His eyes rolled back in his head as he fell to his back. "Fuck. That was...damn. You're good."

She smirked and stood, stripping naked for him. He sat up and slid his pants the rest of the way down, toed off his boots and socks, threw his shirt off, and crooked a finger for her.

She slithered on top of him and he rolled them. "My turn," he commanded as he moved down, down, down, her body.

He returned the favor twice over, enjoying her tart flavor on his tongue as she came before he reached into the pocket of his discarded jeans for the condom. "You ready, sweetheart?"

She bit her lip and nodded before she turned over and put her ass in the air. His eyebrow went up, but he shrugged and went with it. Chick knew what she wanted. He could respect that.

He kissed her shoulders as he slid the condom on and kissed down her spine. She let out a moan of pleasure as he bit both globes of her ass before he kissed back up to her neck. "Do you want it rough? I don't usually do that, but you seem to..."

"Yes!" she cried. "Fuck me hard and leave me bruised."

He blinked. He was no stranger to sex, but usually it was the other way around. He was the one wearing the bruises (not that he was complaining) but still... "If you're sure..."

Instead of answering, she pushed back, impaling her self on his cock. "Fuck," he hissed as he grabbed her hips. He gave her what she wanted, the fuck of her life as he pounded into her while she cursed and bucked. It was one hell of a wild ass ride.

When it was finally over, the long day of hunting, Jordan, the booze, and the excellent sex lulled him to sleep almost immediately, but not before he saw a self-satisfied smirk on her face.

* * *

The next morning, Dean woke alone, which wasn't quite a surprise. He'd gotten used to doing the leaving, but about a third of the time, it was the chick that left. Such was life. He stood and went to find his clothes, which weren't by his side of the bed. _She cleans, too? Wow._

He searched the bathroom, the drawers, under the bed, nothing. He was as naked as the day he was born. And with his clothes... "Son of a bitch!" he yelled. She stole his wallet, his cell phone, everything. "FUCK!"

He looked out the window at the just breaking dawn and sighed. Her car was, naturally, gone. Luckily for him, he was in the same motel as Sammy. So, with a hit to his pride, he wrapped the sheet around his waist and walked barefoot a few doors down and pounded on the door.

Sam opened it wide eyed, gun in his hand. Dean just shot him a look. "Don't fucking ask."

Sam's lip quirked. "Please tell me you at least got laid."

He gave a self depreciating chuckle. "Yeah, I did."

"She take everything?"

"Yes. Damn it. My phone. My fucking phone. I just beat that next level of Candy Crush, too."

"Sucks to be you," Sam chortled as he opened the door wide to allow his brother in.

"Fuck you, Sam. Fuck you." He knew he'd never live this one down. _Man, some days, I fucking hate my life..._


	5. Night Moves

Disclaimer: Still don't own Supernatural. But I can enjoy playing with Dean.

Author's note: This one is a tag to "Baby". We all know what Sam was doing while Dean was in that roadhouse, but what was Dean doing? After all, he said "Mistakes were made." Hehehe...

So, this one is short, sweet, and dirty. An add on to a mini-fic challenge I wrote on Tumblr a while ago...Only made a few changes to the top, but the smut is all new. Enjoy!

* * *

Dean/Reader insert

"Night Moves"

You'd felt his eyes on your ass all night as he drank his beer, schooled some young bucks in pool, and played darts with some of the regulars. Now it was closing time. "Alright, clear out!" you yelled. "Ya ain't gotta go home, but you can't stay here!"

A few of the regulars groaned, but knew not to mess with you. You and your baseball bat had cracked a few skulls. "That means you, too, tiger," you told him as you glanced at the clock. It was three AM and you were bushed.

"How bout you join me?" he asked.

You looked him up and down. Danger oozed from him, charisma too. It had been a long dry spell for you. You shrugged inwardly as you poured a couple of shots. If you were gonna make a mistake tonight, better to do it with a hunk of handsome like him. "I'm y/n."

"Dean," he said as he took your offered hand. His hands were rough, the callouses making you shiver as you imagined them on your thighs. "This your place?"

You downed a shot and shook your head. "No, but it belongs to my buddy. Just watching the joint for him while he's in vacation. Asshole went to Cabo."

"That bastard," he said, making you laugh.

"Yeah, guess he's earned it."

He downed a shot and you did as well before he leaned closer so he was in your face. You could smell the booze on his breath mixed with the scent that was all man. "And what have you earned?" he wanted to know.

You licked your lips and said, "There's a sofa in the back room."

"Bring that bottle of whiskey," he growled, the sound of his gravelly voice going straight to your clit.

You snagged up the bottle and sashayed toward the office. You didn't have to look to see that he'd followed you; you knew he had. Your senses were tingling as your body thrummed with need. You barely breached the door and his hands locked onto your hips as his mouth latched onto your neck.

"God," you muttered.

"Dean," he said in your ear, "But God works."

You turned in his arms and appraised him. He had a smirk on his face a mile wide. You put your hand on your hip. "Pretty damn full of yourself, aren't you, Dean?"

In answer, he picked you up and sat you on the desk. His one hand went to your breast, his other, down to the juncture of your thighs where he palmed your already throbbing clit through your jeans. "Sweetheart, you have no idea."

You licked your lips as your mouth went dry but you cheekily replied, "I'd like to be full of you."

Mischief lit his eyes. "That, I can do."

From there, it was a race to get naked. You needed to touch him. All of him. Usually these kind of hook ups were "insert tab A into slot B" half-clothed, but your hands were itching and his seemed to be, too, because the next thing you knew, you were stripped naked. He eyed you hungrily and you couldn't help but preen a little bit.

"Fuck. You're hot," he managed before he dropped to his knees before you.

You couldn't help it as your eyes widened. Most guys didn't care to go downtown, but this guy, he seemed all too inclined to get you off. He gently pushed your ass toward the desk, hooked your leg over his shoulder, and dove in.

Your hands automatically found purchase in his hair as he began figuring out what made you feel good. It didn't take long. Eight months of doing it for yourself had you screaming within minutes at another person's touch.

When he pulled away, that perma-smirk was on his face again as he declared, "Delicious," almost causing you to lose it. He gently removed your leg from his shoulder and stood, before pulling you with him toward the couch. He dropped down onto it, and bringing you with him, put your knees on either side of his thighs.

There was a fierce need in him now as he growled, "You clean?"

"Y-Yeah," you managed, need clouding your judgement. "You?"

"Sure am. The pill?"

"Shots," you panted as his teeth nibbled on your neck and his hands fisted in your hair.

"Good," he groaned as he thrust and suddenly, holy fucking shit, you were full. You gasped as you stretched and he asked through clenched teeth, "You okay?"

Instead of answering, you began rocking your hips. He caught on quick enough and gripped your hips as you rode your way through another orgasm. When you'd finished, and slid bonelessly to his chest, he chuckled.

You lazily lifted your head. "What?"

"You don't think I'm done, do you?" He picked you up as if you weighed nothing and laid you out on the couch. Instead of jumping right back in, he laved attention on your body, taking time to worship your breasts, paying particular attention to the delicate underside, and you hadn't realized his hands were moving until three fingers curled inside of you.

"Fuck!" you screamed as he brushed your g-spot.

His answering chuckle reverberated against the heated skin of your chest. He got you off yet again before his body covered yours.

Once he had thrust into you anew, he began peppering every inch of you his mouth could reach in kisses, causing your senses to go crazy as your whole body was assaulted by wave after wave of sensation.

The next time he pulled away, you could barely move, but that didn't stop him as he turned you over onto your back. You moved to get up on your knees, but he just held you down and began kissing all over your back. You'd never felt quite so...cherished before.

His hand dipped back into you and you let out a keening wail as he managed to hit your g-spot over, and over, and over again as his thumb massaged your clit until finally you were screaming, "No more! No more!"

That was when he helped you stand on shaky legs to bend you over the arm of the sofa. Your eyes widened slightly as he slapped your ass, but then he was back inside you, pounding you for all you were worth and it was all you could do to hold on as he shoved you over the edge.

The damn man had the stamina of a fucking racehorse as he got you off yet again before he pulled away once more and turned you in his arms. He was all smiles as he asked, "Had enough?"

"Of you? Never, sugar,"

He gave a little nod and led you to lay down on the sofa once more. You were exhausted and sweaty, and damn, you'd had the best sex of your life as he slipped back inside. Your hands wrapped around his neck and your legs around his waist as he finally seemed to be wearing down, then with a growl in your ear, he came, dragging you along with him.

He fell to your side and you turned so there was room on the sofa for you both. Both of you were sticky, sweaty, and sated as he hooked an arm around you and you both fell asleep.

You woke about an hour later to the sound of the toilet flushing and water running. He had covered you with your jacket, you noticed as you sat up.

He walked out of the bathroom and smirked tiredly. "So, uh, I gotta jet..."

You nodded. "Thanks for the ride."

His grin grew. "Trust me. The pleasure was ALL mine."

You watched him go, enjoying the shape of that ass in those jeans before you blew out a breath. Drinks were had, mistakes were made, and you didn't regret a damn one.


End file.
